At the same time, in my other blogs, there are other synthetic methods of this type of compound,92093-23-7, 1-(4-Bromophenyl)ethane-1,2-diol, and friends who are interested can also refer to it.
Adding a certain compound to certain chemical reactions, such as: 92093-23-7, 1-(4-Bromophenyl)ethane-1,2-diol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Safety of 1-(4-Bromophenyl)ethane-1,2-diol, blongs to alcohols-buliding-blocks compound. Safety of 1-(4-Bromophenyl)ethane-1,2-diol
Alternative preparation of chiral 71rans-Lambda/-[2-(4-bromophenyl)cyclopropyl]-2- propanesulfonamide Enantiomer 1 and Enantiomer 2 EPO enantiomer 2enantiomer 1 Intermediate 7 Intermediate 7 enantiomer 2 Enantiomer 1 Enantiomer 2 trans trans; Intermediate 9, Enantiomer 1: chiral 2-(4-bromophenyl)oxirane Enantiomer 1; A 50OmL round bottom flask, equipped with magnetic stirrer, was charged with 10OmL of 1BuOH, 10OmL of water and of AD-mix-beta(30.6g). Stirring at room temperature produced two clear phases; the lower aqueous one appeared bright yellow. The mixture was cooled to 00C whereupon some of the dissolved salts precipitated. 4-Br-styrene (4g, 21.85mmol) was added at once and the heterogeneous slurry was stirred vigorously at 00C for 3h. While the mixture was stirred at 00C, solid sodium sulfite (32.8g) was added and the mixture was allowed to warm to room temperature and stirred for 1h. 20OmL DCM was added to the reaction mixture and after separation of the layers the aqueous one was further extracted with DCM (3x10OmL). Combined organic extracts were dried over Na2SO4 and evaporated to dryness to get 4.9g of crude material as a colourless thick oil.3.9g of this oil (17.97mmol) were dissolved in dry DCM 5OmL, under nitrogen. To this solution trimethylorthacetate (2.962mL, 23.27mmol) was added and the mixture cooled down to O0C. TMS-CI (2.964mL, 23.36mmol) was added dropwise and the reaction mixture left reacting for 1.5h. The volatiles were evaporated and the residue was dissolved in MeOH, treated with K2CO3 (3.1 g) and stirred vigorously at room temperature for 3h. The suspension was filtered, the solid was washed with DCM and the filtrate was evaporated in a rotary evaporator at room temperature under EPO vacuum to get crude title material (3.9g) that was purified by SiO2 flash chromatography eluting with petroleum ether/Et2O from 95/5 to 90/10. Evaporation of the solvent afforded title material, 2.95g, as a colourless oil that became a waxy solid in the fridge. NMR (CDCI3): 7.49 (d,2H), 7.13 (d, 2H), 3.84 (dd, 1 H), 3.13 (dd, 1 H), 2.77 (dd, 1 H). Chiral HPLC: ee 98.6% Analytical Chiral HPLC conditions: column: CHIRALPAK AS-H (25×0.46 cm) mobile phase: n-Hexane/Ethanol 95/5% v/v flow rate: 1 ml/minUV wavelength range: 200-400 nm Rt Enantiomer 1 : 6.1 min 99.3 a/a% Rt Enantiomer 2: 8.5min 0.7 a/a%.
At the same time, in my other blogs, there are other synthetic methods of this type of compound,92093-23-7, 1-(4-Bromophenyl)ethane-1,2-diol, and friends who are interested can also refer to it.
Reference:
Patent; GLAXO GROUP LIMITED; WO2006/87169; (2006); A1;,
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